Filmmaker Douglas Keeve (Unzipped and Seamless) turns his attentions from the fashion industry to a famous New York City landmark that's undergoing a controversial renovation in this portrait of the legendary Gramercy Park Hotel. In it's early days, the Gramercy was a high-society hot spot - the Kennedys once rented out an entire floor, and a young Humphrey Bogart exchanged his wedding vows there. Later, in the 1970s and 80s, musicians, artists, and junkies haunted the hallways, attracted by the management's "anything goes" policy as well as the Gramercy's affordable room prices. Now, as luxury hotelier Ian Schrager prepares for the grand re-opening of the iconic Hotel Gramercy Park, director Keeve attempts to find what kind of impact this posh renovation will have - positive or negative - on the hotel's notorious reputation as a seedy-chic hotspot. Some residents refused to leave during the construction, and many neighbors resent the glossy makeover that the Gramercy is getting. In addition to speaking with the people who live and work at the Gramercy, Keeve also explores the sometimes-tragic story of the Weissberg family. The Weissbergs have owned and lived in the Hotel Gramercy Park for fifty years, and experienced their fair share of both joy and heartache within its walls. As the Weissbergs reflect on the legacy of the Gramercy, viewers are offered an intimate and comprehensive reflection of a place that has become known as a virtual beacon for the creative and cultural elite.